title: Cascade fluorofunctionalisation of 2,3-unsubstituted indoles by means of electrophilic fluorination.
abstract: Cascade fluorofunctionalisation of 2,3-unsubstituted indoles featuring the formation of C-C, C-F and C-O bonds via electrophilic fluorination using N-fluorobenzenesulfonimide is described. The use of an O-nucleophile tethered to the nitrogen of indoles enables the synthesis of polycyclic fluorinated indoline derivatives from simple precursors in 40-63% yields.
authors.affiliation: Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8, Biomedical Grove, Neuros, #07-01, Singapore 138665, Singapore. nguyen_minh@ices.a-star.edu.sg duong_hung@ices.a-star.edu.sg.
authors.forename: Tuan Minh
authors.initials: TM
authors.lastname: Nguyen
authors.forename: Hung A
authors.initials: HA
authors.lastname: Duong
authors.forename: Jean-Alexandre
authors.initials: JA
authors.lastname: Richard
authors.forename: Charles William
authors.initials: CW
authors.lastname: Johannes
authors.forename: Fu
authors.initials: F
authors.lastname: Pincheng
authors.forename: Danson Kwong Jia
authors.initials: DK
authors.lastname: Ye
authors.forename: Eileen Lau
authors.initials: EL
authors.lastname: Shuying
mesh_terms: D002244:Carbon / Q000737:chemistry; D003500:Cyclization; D005461:Fluorine / Q000737:chemistry; D054879:Halogenation; D007211:Indoles / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry; D013696:Temperature; D000096926:Benzenesulfonamides
chemical_list: D002244:Carbon; D005461:Fluorine; D007211:Indoles; D010100:Oxygen; D013449:Sulfonamides; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides; C057812:indoline